Dextroamphetamine

Clinical dataPronunciationTrade namesDexedrine, Zenzedi, othersOther namesd-Amphetamine, (S)-Amphetamine, S(+)-AmphetamineAHFS/Drugs.comMonographMedlinePlusa605027License dataPregnancy
categoryDependence
liabilityPhysical: None
Psychological: ModerateAddiction
liabilityModerateRoutes of
administrationBy mouth, transdermal, intravenous, insufflation, rectalDrug classStimulantATC codeLegal statusLegal statusPharmacokinetic dataBioavailabilityOral: ~90%Protein binding15–40%MetabolismCYP2D6, DBH, FMO3Metabolites4-HydroxyamphetamineOnset of actionIR dosing: 30–45 minutes
XR dosing: 1.5–2 hoursElimination half-life9–11 hours
pH-dependent: 7–34 hoursDuration of actionIR dosing: 3–6 hours
XR dosing: 8–12 hoursExcretionKidney (45%); urinary pH-dependentIdentifiersCAS NumberPubChemCIDIUPHAR/BPSDrugBankChemSpiderUNIIKEGGChEBIChEMBLCompTox Dashboard(EPA)ECHA InfoCard100.000.103Chemical and physical dataFormulaC₉H₁₃NMolar mass135.210 g·mol3D model (JSmol)ChiralityDextrorotatoryenantiomerDensity0.913 g/cmBoiling point201.5 °C (394.7 °F)Solubility in water20mg per ml(verify)

Dextroamphetamine is a central nervous system (CNS) stimulant and enantiomer of amphetamine that is used in the treatment of attention deficit hyperactivity disorder (ADHD) and narcolepsy. It is also used illicitly to enhance cognitive and athletic performance, and recreationally as an aphrodisiac and euphoriant. Dextroamphetamine is generally regarded as the prototypical stimulant.

The amphetamine molecule exists as two enantiomers, levoamphetamine and dextroamphetamine. Dextroamphetamine is the dextrorotatory, or 'right-handed', enantiomer and exhibits more pronounced effects on the central nervous system than levoamphetamine. Pharmaceutical dextroamphetamine sulfate is available as both a brand name and generic drug in a variety of dosage forms. Dextroamphetamine is sometimes prescribed as the inactive prodruglisdexamfetamine.

Side effects of dextroamphetamine at therapeutic doses include elevated mood, decreased appetite, dry mouth, bruxism, headache, increased heart rate, insomnia, anxiety, and irritability, among others. At excessive doses, psychosis (i.e., hallucinations, delusions), addiction, and rapid muscle breakdown may occur. However, for individuals with pre-existing psychotic disorders, there may be a risk of psychosis even at therapeutic doses.

Dextroamphetamine, like other amphetamines, elicits its stimulating effects via several distinct actions: it inhibits or reverses the transporter proteins for the monoamine neurotransmitters (namely the serotonin, norepinephrine and dopamine transporters) either via trace amine-associated receptor 1 (TAAR1) or in a TAAR1 independent fashion when there are high cytosolic concentrations of the monoamine neurotransmitters and it releases these neurotransmitters from synaptic vesicles via vesicular monoamine transporter 2 (VMAT2). It also shares many chemical and pharmacological properties with human trace amines, particularly phenethylamine and N-methylphenethylamine, the latter being an isomer of amphetamine produced within the human body. It is available as a generic medication. In 2023, mixed amphetamine salts (Adderall) was the 15th most commonly prescribed medication in the United States, with more than 32million prescriptions.